Your Stress-Free Holiday Planning Guide

Productivity

Oct 1

Keep reading this post to learn:

5 stress-free steps to plan out your upcoming holiday season
What to do so you can be more intentional and enjoy your holidays even more this year

Before I really get into it, I wanna start off by saying that I know there are sooo many holidays out there and I respect your decision to celebrate whichever ones you want. I’ll mostly be focusing on the holidays that I partake in but the frameworks I use to plan and prep for them can be applied to any holiday – just make what I’m sharing work for you!

So, I don’t know if you feel the same but quarter 4 feels like a whirlwind… October-December is packed and happens so fast. The holidays tend to sneak up on us as we’re juggling different roles to manage our day-to-day lives. Like life doesn’t chill out just because the holidays arrive and adding the holidays on top of your already full life can make things feel overwhelming really fast.

I used to have the highest hopes for the holiday months. When October hit, I would be so excited about all the memories I wanted to make doing fun holiday stuff but then I’d blink and it’d be Halloween and I was trying to haphazardly throw together a costume with what I already had in my closet and I’d promise myself that I’d be better prepared for Thanksgiving festivities. And the cycle would repeat – each holiday would arrive and I’d be so wrapped up in day-to-day life that I put off intentionally prepping and I’d wind up frustrated that another holiday had come and gone with me feeling stressed out scurrying around instead of enjoying making memories.

Well listen – that is not gonna be our journey this year okay? We are going to be intentionally prepared for October-December this year so we can enjoy the holiday season with little to no stress and be happy about the memories we made with our loved ones when January rolls around. We’re going to create a plan for all of the important upcoming holidays to avoid scrambling at the last minute.

The way I’m gonna outline this blog post (and podcast episode if you would rather listen in!) is by sharing the exact steps that I follow while prepping for all the holidays in quarter 4. My hope is that you listen to it today and then maybe this weekend you can spend an hour or 2 doing it for yourself so that you have ample time to prep for the holiday season ahead.

YOU WILL NEED:

- Your planner/Google cal/whatever you use to keep track of important dates

- Somewhere to brain dump (a notebook or Google doc)

- The tool you use to organize lists, tasks, and reminders (I use my Peacefully Productive Planner, Google Cal, and Notion…I’ll link an episode in the show notes that walks you through how I plan and organize my whole life using these tools)

AND HERE IS WHAT YOU ARE GOING TO DO:

Step 01: In your brain dump space, write out all of the October-December holidays you want to create an intentional plan for.

You’ll obviously need to use the tool that you use to keep track of important dates to help you find these. I personally use a notebook to do all of my brain dumps (the one we sell on hustlesanely.com actually). I like to give each holiday its own page in my notebook as I’m doing my holiday planning.

The holidays that I want to intentionally plan for this year between October-December are:

– Halloween
– Adam’s birthday
– Thanksgiving
– Everly’s birthday
– Christmas

So step 01 - easy, right? Just list out all the holidays you want to plan for.

Step 02: For each holiday, define 1-5 non-negotiables and put them on your calendar when applicable.

The way I do this is I ask, “What matters to me for this holiday?” Clearly defining what matters to you for each holiday, helps prioritize these things. It can be easy to get swept up in the “do all the things” for every holiday trap but that’s stressful. I find it so beneficial to name 1-5 things that matter for each holiday so you are a better steward of your yesses and can more easily say “no” to things that don’t match up with your non-negotiables. Don’t be tempted to make this into a to-do list for each holiday – that’s coming up. This is just for you to name what is the most important to you for each holiday.

I’ll give you a few examples of my non-negotiables for each holiday that I’m planning for:

– Halloween non-negotiables:
01: Dress up in a fun family costume
02: Visit our family in said costumes
03: Visit a pumpkin patch
04: Decorate the front porch for Halloween
05: Go to Creatures of the Night at the Zoo

– Adam’s birthday non-negotiables:
01: Plan a small gathering for friends to celebrate

– Thanksgiving non-negotiables:
01: Blue Ridge Trip
02: Family meal on Thanksgiving
03: Light Up Blue Ridge on Black Friday

– Everly’s birthday non-negotiables:
01: Plan a family memory experience to celebrate
02: Plan an extended family dinner to celebrate

– Christmas non-negotiables:
01: Decorate the house for Christmas
02: Family baking night with matching family PJs
03: Christmas movie board
04: Go to Busch Gardens Christmas Town
05: Spend Christmas Day at home with extended family

These don’t have to be the ONLY things you do during each holiday but these are the most important to you.

Step 03: For each holiday, brain dump everything that needs to be done to prep for the holiday, paying special attention to your non-negotiables.

This is where we start jotting down all the to-dos for each holiday. We’re gonna call these your holiday prep lists. The way I like to do this is just getting everything out of my head and onto my brain dump paper. I don’t care how messy or long the lists are - I use the next step to organize and assign dates to tasks. The purpose of this step is literally just to get the tasks out of my head.

Each holiday gets its own task list and I start by writing out any tasks I need to do to make my non-neogitables happen and then I start writing other tasks that pop in my head that need to be done for that particular holiday.

Some examples:

Halloween tasks:
- Decide on and purchase costumes
- Get decor down from the attic and put it up
- Buy tickets for the Creatures of the Night event
- Check pumpkin patch hours and plan date of visit
- Decide what time we’re going to my family’s on Halloween
- Buy film for Polaroid camera
- Buy candy for Halloween night
- Make sign to put out with Halloween candy while we are gone

Thanksgiving tasks:
- Make packing list for Blue Ridge Trip
- Pack for Everly and I
- Decide what side dish we are cooking for Thanksgiving
- Prep Jeep for road trip
- Prep Everly’s travel activities/snacks
- Check sizes of Everly’s cold weather clothes and buy what’s needed to fill in the gaps

Christmas tasks:
- Get decor down from the attic, sort it, and buy anything to fill in the gaps
- Decorate!
- Order matching family PJs
- Choose dish for family bake night and plan when it will be
- Make 2024 Christmas movie board
- Buy tickets for Christmas Town
- Plan menu for Christmas Day
- Make list of Christmas gifts to buy (don’t forget the mail carrier and neighbors)
- Stock up on wrapping supplies
- Make Everly’s gift wish list for family
- Complete Christmas shopping by December 15

Step 04: Looking at each holiday’s prep list, assign the dates you’re going to do the tasks and put them in your task management tool.

As you do this step, remember that you’re the boss of your schedule. You are doing this holiday planning early enough that you can space tasks out and not be frantically trying to do stuff at the last minute. Schedule things so that you have plenty of wiggle room in case you need it.

So for me, this would look like taking each holiday’s prep list from the last step, pairing tasks together that make sense, and putting them into Google calendar (I use Google calendar to manage my tasks).

I’ll use my Halloween task list as an example to share with you:

- Decide on and purchase costumes
I know I usually do life admin tasks on Fridays and Mondays so I’d put this on my Google cal for October 4 since it’s an early Friday in October which means I have plenty of time to make a choice and buy the costumes

- Get decor down from the attic and put it up
I’d put this on my Google cal for October 1 because Adam refuses to let us decorate earlier, lol

- Buy tickets for the Creatures of the Night event + Check pumpkin patch hours and plan date of visit
I paired these tasks together because they both require calendar planning. I’d put these tasks on my Google cal for October 4 because I know I want to do the pumpkin patch earlier in October so we can get pumpkins for our porch and I need to get tickets for the Creatures of the Night event before they sell out later in October. So then on October 4, when I see these tasks on my Google cal, I’d plan what day we are going to the pumpkin patch based on when the one near us is open and put that in our shared family Google cal and then I’d look at the dates the Creatures of the Night event is running and buy tickets as close as I could to Halloween and add that date to our shared family Google cal

- Decide what time we’re going to my family’s on Halloween
Since Everly is young and we aren’t trick or treating yet, this doesn’t take much thought/planning so I don’t need an assigned date to sit and do the planning. We will just be driving to my parent’s house so they and my grandparents can see us in our family costumes and take our picture, lol. Since Halloween is on a Thursday, I’ll take off work an hour early, so 3, so we can get ready and leave our house by 3:30 to go to my parents so we can be back in time for Everly to go to bed around 7/7:30…so I’d just pop that in our shared family Google cal

- Buy film for Polaroid camera + Buy candy for Halloween night
I paired these together because I can get both of these things from Target or I can order them both on Amazon at the same time – I’d put this on my Google cal for October 7 so that there is plenty of time for the items to arrive…because let’s be real, I’m ordering off Amazon, lol

- Make sign to put out with Halloween candy while we are gone
I’d put this on my Google cal for October 28 - the Monday before Halloween

With these tasks assigned to certain dates in my Google cal, I’ll see them every week when I’m sitting down with my Peacefully Productive Planner for my Weekly Prep Meeting – so that when I’m deciding my Weekly Top 3 Tasks and daily Focus 3 tasks, I see these things and can make sure they get done.

A little pro tip: for tasks that are recurring every year, mark them as “recurring” in your task management system so they automatically pop up on your task list every year. There is also a spot in Peacefully Productive Planners to keep track of recurring tasks if you prefer to do it that way!

Step 05: Add some breathing room to your calendar.

Holidays take up a lot of energy – I don’t know about you, but I don’t want a full day of meetings the day after Christmas. Talk about a buzzkill, lol. That’s why the last step is going into your calendar and blocking off some margin. Another way to view margin is intentional white space. Space you are leaving unscheduled on purpose so you can lean into rest and being present.

Maybe for you that looks like taking off of work the day before and the day after Christmas. Or taking the entire week off of Thanksgiving.

If you’re an entrepreneur, block these days off on your calendar now so you and your clients/team/whoever have plenty of time to know that you’ll be off during those dates.

If you work for someone, put your vacation time requests in now so you have plenty of time to get them approved.

A surefire way to feel stressed out during the holidays is by cramming too much into your calendar and feeling spread thin - adding some breathing room to your calendar can help with this!

Now remember – our schedules and routines are tools, not chains. Everything you planned is not set in stone…life happens, things change and that’s okay. Use these plans as a guide, not as an anchor. Learning how to be flexible and be able to adapt to shifts is such a valuable skill.

And there you have it! Your stress-free holiday planning guide! I hope it was helpful and gave you a solid plan of action to intentionally prep for the holidays now so you aren’t running around trying to plan everything at the last minute!

HAVE YOU HEARD?